Thioanisole → 6-Methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolinol

HRID 387855Notes

Reaction equation

HRID 387855 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([S:19][C:20]3[S:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29])C1C=CC=CC=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:29][O:28][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[S:19][C:20]1[S:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 589312112-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]sulfanyl}-5-nitrothiophene

Product 1

HCID 1359899586-Methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolinolYield 85.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-(Benzyloxy)-6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]quinoline (4.0 g), trifluoroacetic acid (40 ml) and thioanisole (4 ml) were stirred together at 65° C. for 2 hours. The mixture was returned to room temperature, the solvent was distilled off under reduced pressure, 80 ml of methanol was added to the residue, and then bicarbonate water was added until the foaming subsided. The precipitated solid was filtered out to obtain 2.7 g of a yellow powder.

Workup

  1. customwas returned to room temperature
  2. distillationthe solvent was distilled off under reduced pressure, 80 ml of methanol
  3. additionwas added to the residue
  4. additionbicarbonate water was added until the foaming
  5. filtrationThe precipitated solid was filtered out

Sources & evidence

ORD record
ord-6783fb8da877465aa3c6bdcbfec98a04
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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